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The young art career of Jackson Tupper began at the University of Vermont, and despite the fact that he majored in studio art, his style really took shape while he was bored in math class.

Tupper doodled in his freshman logic class at UVM, and it was there that one of the characters that populated his early artistic creations made his first appearance. The images in his work only grew weirder and wilder after that.

“I was kind of obsessed with killing things in my illustrations,” Tupper said. “A lot of my illustrations at that time were kind of dark, but they had this combination of being dark and adorable at the same time. That was something I was fascinated by because of the reaction people had when they saw it – ‘Oh… that’s… really… cute….’”

The murderous moments have waned, but much of Tupper’s evolving art still straddles that line between friendly and frightening. The 22-year-old whose work has been displayed prominently throughout Burlington receives his first solo gallery show when his exhibit of new work, titled “Oh Um Ah,” opens Friday at the New City Galerie and runs through Jan. 28.

The gallery’s organizing director, Joseph Pensak, is excited to be hosting the show, partly because he sees it as a nice coup for the 2-year-old Church Street space, but more so because he thinks Tupper deserves to be seen.

“As young as he is and to have this amount of talent is pretty remarkable,” Pensak said. “When I talked to him about doing a show I couldn’t believe he hadn’t done a gallery show in Burlington.”

Tupper first displayed his art publicly in Burlington at The Skinny Pancake eatery two years ago. “That was my first show and I didn’t really know what to expect. After that show I was surprised how easy it was for me to get shows in town, which I think is partly that Burlington has such a great art scene and there are so many cafes that want local art,” Tupper said. “That was cool to find out my art had a demand, which was something I wanted to happen but didn’t expect to happen so fast.”

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He followed with exhibits at UVM’s Davis Center, the August First Bakery and Radio Bean coffeehouse and was asked last year to create illustrations directly on the interior walls of the new music venue Signal Kitchen. The latter was a big, bold project featuring sharp black-and-white lines, anthropomorphic animals and scruffy humans that called much of the community’s attention to Tupper’s work.

“It’s really exciting for me because for the past two years I’ve been in the circuit of showing at cafes like Radio Bean,” Tupper said by phone last week from suburban Richmond, Va., where he was working on pieces for his New City Galerie exhibit in a barn owned by his girlfriend’s family. “For me it’s kind of time to move on to the next step. Having a solo gallery show, it’s comforting to know all this hard work is actually going somewhere.”

Tupper’s propensity for drawing began in his childhood in Kennebunk, Maine. “I was very much into reading ‘Calvin and Hobbes’ comic books and trying to copy cartoon characters,” he said. “All through school my assignment planners and my notebooks and stuff were just covered with doodles.”

Tupper has been into snowboarding since he was 6 and has long wanted to create designs for snowboards; the proximity of ski resorts and the presence of the Burton Snowboards headquarters in Burlington helped draw Tupper to UVM. His style of art has been shaped by snowboard designs and also by graffiti-inspired art by the likes of Barry McGee and McGee’s late wife, Margaret Kilgallen.

His art, which sometimes features random objects coming out of people’s heads, also evokes “Monty Python” illustrator Terry Gilliam, a reference Tupper said he has heard a few times but hadn’t previously considered. “I think there are a lot of things in my subconscious I draw without ever really thinking about it,” Tupper said, noting that the similarly surreal Salvador Dali has been an inspiration.

Pensak, the director at New City Galerie, said Tupper’s skill at creating strongly defined characters makes his work stand out. “In some ways it defies categorization. I definitely see his work tying together with this really talented group of people making band posters, just great designers,” Pensak said, mentioning indie-rock poster illustrator Jason Munn as an example.

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He also sees a comparison between Tupper’s work and the growing field of graphic novels. “That’s the other thing I like about his work,” Pensak said. “It’s so good it belongs in a gallery, but it has a broad appeal and it’s so fun.”

Tupper said he’s looking for jobs in illustration or graphic design but ideally will become a studio artist who shows and sells his art. He’s hoping the Burlington exhibition gives him a strong push toward that. In the meantime, he’s excited to give people the chance to experience his work through the New City Galerie exhibition.

“I like people to kind of just enter into the world that I create,” Tupper said. “A lot of my paintings just kind of explore a narrative which isn’t specific. You can’t exactly say what’s going on, but it’s just this imaginative world. I want people to be drawn into that world and experience it.”

The name of the exhibit, Tupper said, gives a little insight into the effect he hopes his art has on people. “The title of my show is ‘Oh Um Ah,’” he said. “It means several things to me, but one of them is about the expression of wonder.”